4-Quinolinecarboxylic acid → HCID 71655554, compound

HRID 528679Notes

Reaction equation

HRID 528679 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[NH2:62][CH2:63][C:64]([N:66]1[CH2:70][CH2:69][CH2:68][C@H:67]1[C:71]#[N:72])=[O:65]>CN(C=O)C>[C:71]([C@@H:67]1[CH2:68][CH2:69][CH2:70][N:66]1[C:64](=[O:65])[CH2:63][NH:62][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)=[O:13])#[N:72]

Participants

7

Reactant 5

HCID 102434-Quinolinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 89705144HCID 89705144, compound

Product 1

HCID 71655554HCID 71655554, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Commercially available quinoline-4-carboxylic acid (0.078 g, 0.449 mmol) was dissolved in 7 ml of DMF, N-ethyl-N-isopropylpropan-2-amine (0.242 ml, 1.347 mmol), HOBT (0.069 g, 0.449 mmol) and TBTU (0.144 g, 0.449 mmol) were added. After 15 min a solution of (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (0.120 g, 0.449 mmol) (prepared as described under A.1 of the experimental part) in DMF was added. The mixture was stirred overnight at room temperature. The volatiles were evaporated, the residue was dissolved in ethyl acetate and extracted with 1 N citric acid, saturated sodium bicarbonate and brine. The solution was dried over sodium sulfate, filtrated and evaporated. It was purified using column chromatography (1-5 hexane-ethyl acetate).

Workup

  1. additionwas added
  2. customThe volatiles were evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionextracted with 1 N citric acid, saturated sodium bicarbonate and brine
  5. dry with materialThe solution was dried over sodium sulfate
  6. filtrationfiltrated
  7. customevaporated
  8. customIt was purified

Sources & evidence

ORD record
ord-5d99de7a73214fa9b803bbbe9943db91
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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